All The Way
by CanadianChick07
Summary: Hailey gets a surprise job offer from the DEA and ends up at Jay's to talk about it. The beginnings of Upstead.
1. Chapter 1

Hailey Upton took a deep breath as she walked up the steps to the house of her Sergeant's home. Usually she didn't mix business with after hours, except her one time fling with Adam Ruzek, and her drinks with her partner. She didn't really consider drinks with her partner mixing business with pleasure, because it was what made it get them to work the next day. It was what worked.

She had never been to Hank Voight's home. After Lindsay had left Chicago, Christmases at his house kind of stopped. With Olinsky gone as well, there wasn't much family for Voight. Olive had taken her and Justin's baby to Arizona and Hailey had only heard of her name mentioned once, that was it. She felt for her boss because he had a huge heart under his rusty exterior and somewhat shady ways. One thing was sure, Hailey knew Hank Voight would go to bat for her when push came to shove, and that's why she was on his team.

She sucked in her breath and knocked on the door, loudly, like she would on a suspect's door. Voight opened it up and chuckled as he opened the screen for her. "You don't have to break down my front door," he greeted.

She stepped inside and kicked off her flip flops. It was winter, but she was in shorts and a tank top, just coming from the gym and working out with Antonio and Kim. "Force of habit," she said.

Voight held a hand out and gestured to the living room as he went and grabbed another glass for her and poured a bourbon for her. "Figured you'd end up here eventually."

She raised an eyebrow as he handed her the glass. "Excuse me?"

"Lynch called me a couple weeks ago when they were first digging around on you. Are you surprised?"

She sipped slowly, having the bourbon hit slowly. "Not at all."

She was sitting down on the couch so Voight sat across from her in the loveseat, the TV, having C-SPAN on. "So you're here because they made you an offer."

Hailey took another sip of her alcohol. He poured a stiff drink. "They made me a damn good offer."

"Are you going to take it?"

She just looked at him.

"The fact that you're on my door step at 9 pm says that you're seriously thinking about taking the offer and I'm gonna either need to pry Rixton out of Narcotics again or find someone else."

"Morrison from Vice would be a good choice."

"Morrison and Halstead get a long a little too well for my liking," Voight muttered.

She chuckled. "Yeah, I know." She and Morrison went back to their high school days in Chicago and she knew Voight wasn't sure about Morrison's stability as well. Like Jay, he had a hard time transitioning from Iraq.

Voight took a sip of his own bourbon. "Lynch really wants you."

"Lynch also has a stick up his own ass and you know that. He's going to tell me what I want to hear so I take the job."

"The Special Agent in Charge of Chicago Division doesn't just offer jobs to people on a whim," Voight pointed out.

Hailey took a deep breath in. "It's not the first job offer."

Voight shrugged. "And it won't be the last, Upton. You're a good Detective."

"So what you're not saying is that if I turn down Lynch, other agencies are going to still offer me jobs?"

He finished his drink. "Why the hesitation?"

"The last time I left Chicago for a job, it did not end well," Hailey pointed out.

Voight remembered that the Booth op was technically FBI operated and she was right to have some hesitation leaving the safety of the Chicago Police Department. "Looks like you have some thinking to do."

She finished her drink. "Lynch say anything else?"

He shook his head. "More interested in your undercover skills."

Hailey knew that part of the plan but Voight didn't need to know. "Thanks for the drink."

"Am I going to find your resignation letter on my desk tomorrow morning? I do appreciate the heads up," Voight asked as she stood up to leave.

"I don't know. Like you said, I have some thinking to do," she said, shoving her feet in her flipflops.

She was halfway out the door when Voight's voice stopped her. "If you do take it, talk to your partner first."

"Why?"

"The last time he had a partner take a job for a federal agency, she left without a word. He deserves you telling him why," Voight said.

She nodded at her boss. "Yeah, he does."

That made her think as she walked to her truck and clicked the remote start. She had every intention of going back to her own place, having a really hot shower, and thinking about jumping off a cliff for Lynch. But instead she found herself turning down the streets to Jay's condo. This was going to be an even harder conversation that the one with Voight. Much harder.

She had a key to his condo and a fob so she let herself in the front door and took the stairs two by two to his second floor condo. She had never showed up unannounced before so she hoped to God she wasn't interrupting something. She waited like five minutes outside his door before finally getting the balls up to knock softly on it.

He opened the door in sweats and no shirt on and his eyebrow raised. She forced herself to breath. "This is a surprise," he took note of her gym attire as well.

She stepped inside. "Yeah, well."

"Your breath smells like bourbon. How many drinks have you had Hailey?" He said, accusingly.

She glared at him. "One."

He swallowed hard and headed for the fridge. "I have a feeling like I'm going to need a lot of alcohol with where this conversation is going. Why don't you start with where you were?"

She took the beer he offered as they made their way to the couch. Blackhawks vs Sharks game was on. "Antonio's boxing gym with Kim. You know how I go there every Monday."

Jay felt a little bit of an idiot for forgetting that one because they didn't workout together on Monday's because she went there. Sometimes he went there but usually Kim and Hailey went together. Hailey was actually a pretty good boxer but that wasn't surprising and Antonio was showing Kim how to box. "And where'd you go drinking bourbon? Because I know you and you aren't a bourbon girl."

"Voight's."

Now that through Jay in for a loop as he put the shirt that was hanging on the back of his couch back on. "Why were you at our boss'?"

Hailey started ripping the label off her beer. She had absolutely no idea if she was going to take the job or not, but Voight was right; Jay deserved to hear it from her, first. "I got a job offer."

He turned to completely face her. "What?!"

She sucked in her lips and let out a deep breath. "DEA. They want me to do 9 months in Afghanistan and then a long term undercover op."

He was silent as he tried to process this all. Hailey in Afghanistan? It wasn't that she wasn't competent, because she was, but for God's sakes he did not want her over there. He wanted to protect her from the horrors he saw. He knew she wouldn't see them as much as a DEA Agent but still. And that wasn't even touching half of what his brain was thinking.

"Jay, say something, please," Hailey pleaded.

He took a long sip of his beer. "How long have they been recruiting you?" he tried to think of a timeline but damn, the girl was good. She had been acting a little off the past couple days but he hadn't thought much of it. A major job offer from the DEA would do that to a person though.

"Not long. They approached Voight a couple weeks ago when they started digging around about me but they never formally approached me until last week and even then it was informal until tonight."

"At the Thompson crime scene? Chris Lynch? Really?"

Hailey rolled her eyes. "I know. He's a complete ass but he's the SAC of Chicago and he made me a damn good job offer."

Jay took another sip of his beer before shaking his head. "Fuck you, Hailey. Why are you being selfish, not thinking of your entire team that your leaving behind and fucking even thinking about this?"

She put down her beer. "Oh! And fuck you too, Jay! Fuck you. Sorry for thinking about my fucking career!" She expected this response. She truly did and she was prepared for it. She was prepared for emotional Jay and she was ready for it and prepared to fight back as well.

"And the rest of us?"

"I just got a once in a lifetime job opportunity. No, congrats Hailey?"

He stood up and grabbed another beer out of his fridge. He took a look at her finishing hers grabbed a second and handed it to her as he sat down. "Don't fuck with me Upton. I know there's been other job offers. You're too good for other people to not be interested in you."

She looked at him and shook her head. "I don't get you. Did you know Lynch made me a job offer? Did Voight tell you?"

He shook his head. "I had my suspicions the minute Chris Lynch appeared at our crime scene. I know the FBI made you an offer last year."

Hailey took a deep breath. "I'm not Erin Lindsay."

His eyes were furious. "Why the fuck are you bringing her into this?"

"I know she took that damn job with the FBI in New York, ran away and left you without a word. I'm not Lindsay."

"Why are you bringing this up?" He was furious for bringing Lindsay into this conversation.

She looked at him. "Either way, I was going to tell you about the job offer. They just actually made me the formal one tonight. All the other conversations have been off the record. Jay, I don't run. I am not her so stop thinking I am. Stop. I am not leaving without a word or running off into the night. We're having an adult conversation, so start acting like it."

He was still glaring at her. "Nice to know I matter."

"Of course you matter. Why do you think I'm here?"

"What about FLETC?" He asked randomly. All federal agents had go through the federal law enforcement training center in Brunswick, Georgia.

She shrugged, taking a sip of her beer. "Already did my time there."

"Impressive. I guess this is why you have multiple federal law enforcement agencies pounding your door down?"

She shrugged again. "I don't know."

He sat back against the couch. "Is DEA really what you want to do?"

"I don't know what I really what, to be honest."

He sat there for a minute. "Afghanistan isn't a picnic, even as a DEA Agent, although you're not dumb and I know you know that. And then to go long term undercover? That's seriously fucked up. You gotta think about this, Hailey."

"They need me, Jay."

He shook his head. "Not like this, Hailey."

"What are you saying, Jay?"

He finished his beer and went to go grab the whiskey. He looked at her and she just nodded. She knew she was way past the point of driving, so what was another drink at this point? "You either go to Afghanistan or you go undercover, but don't do both and don't do it back to back. Take it from me, Hails. That shit fucks with you mentally. I've done both. Please, take it from me."

That was one of the only times he called her by her nickname, and it was generally either when he wanted to get a point across or as a term of endearment. "Why'd Lynch offer it to me then?"

He handed her a Jack Daniels and coke. "Because you've already done FLETC, you're a good cop and you have the undercover skills. He's not watching out for your mental state when you get back from that hell hole and three weeks later, you have to be someone else for a year. Hails, he's sending you on a suicide mission. You might be in the wire the whole time in Afghanistan but let me tell you, that shit gets to you."

"So you don't think I should take this job?"

"I think Chris Lynch is an absolute bastard," Jay said.

She rolled her eyes. "Not helping, because I already knew that."

"What do you want?"

She shrugged. "I have no idea."

"Do you want to even leave Chicago? You haven't said anything lately about wanting to leave?"

She slowly took a sip as she thought about her words carefully. "No. I finally have it somewhat good. I have a good unit, I don't want to kill my family more often than not which is impressive, I have friends outside of CPD finally, there's you."

"Me?"

She didn't really want to bring up Lindsay again because that didn't end well the first time, although he did need to be told that he needed to have this conversation like an adult. "We've got a good partnership going on, I don't want to fuck that up and leave."

He was silent for a couple seconds and then turned to her. "So don't sell your soul to Chris Lynch and stay in Chicago."

"It's not that easy, Jay."

He looked at her. "Hails, it is. You have FLETC under your belt, you're a good cop and working under Voight gives you a hella lotta street cred in this business."

She nodded. "Fair point." It did. Lynch brought that up as a factor. It was also a downside but more of an up than anything. Voight expected the best under his people and Intelligence had an exceptional close record in CPD because of that. '

"There's going to be other jobs. Maybe some other Lynch's along the ways but maybe someone who will actually give you what you want."

She sighed. "Yeah. Turning down a job like this though…"

Jay looked at her. "Are we going to dance around us?"

She looked at him. "Jay," she warned.

"I don't see you talking about jumping off a cliff for Chris Lynch to your family. You're here."

"You're my partner. Of course I'm going to be here, talking this shit out with you!"

He laughed quietly and sipped his whiskey. "Voight told you to come, didn't he?"

She just looked at him. "I think it was his way of saying to work shit out between us."

"So I think we need to work shit out. I don't want you to leave. There, I said it."

Hailey put her head in her hands and took a few deep breaths before she drank her drink. She could barely look at him but she did. "Personally or professionally?"

"Both."

She downed the rest of the drink and went into the kitchen to make more. Thankfully he left both the coke and the whiskey on the counter. "I don't even know how we do this Jay."

"I don't know either."

"Do you want to try? Because if you don't, you can walk right out this door and we can pretend this conversation never happened," he said, getting off the couch and approaching her as she was mixing her drink.

She swallowed hard and knew she had to make up her mind. "Yes. But, if we do this, we do this all the way."

He laughed a little. "Yeah, no question about that." And then he put his arms around his partner and held her for a second before tipping her head back and kissing her. He had wanted to do that for awhile but who knew that it would take a serious job offer and her almost taking it for them to decide that they wanted to be with each other, on and off the job.

 **AN: I am still not entirely sure if this will be a one shot or story. Thoughts?**


	2. Chapter 2

Jay came out of his room the next morning to see Hailey eating cereal, drinking coffee and scrolling through her phone on his couch and he just chuckled. Clearly she was comfortable enough to be eating breakfast without him, but in reality, he wasn't a morning person lately, and on more than one occasion, she'd just start rummaging through his kitchen, finding something to eat while waiting for him before hitting the gym or going on a run. "Are you going to go home first?"

She shrugged. "Probably. Although I have enough clothes in my truck and your truck that I probably don't need to." That was evidenced by the fact that she was wearing a clean pair of gym clothes of hers and it was at his house. She tried to think of how that happened but couldn't, she was just thankful for clean clothes.

He made himself a cup of coffee from his Keurig and mentally made a note for himself to go grocery shopping because he was running out of the pods. "Not working out this morning?"

She shook her head as she finished her cereal and went to go put it in the dishwasher. "Told Allie I'd workout with her if we are done at a decent time tonight."

"Allie?"

"Detective Allison Montgomery from Narcotics?" Hailey prompted Jay. She knew he knew of her but he probably had never heard of her being called Allie.

Jay took a sip of his coffee. "I didn't know you were friends. At all. Or at the working out together stage. And where has she been lately?"

"She just finished a 18 month long undercover," Hailey said, arching an eyebrow.

"You have fun with that one," he said, taking another sip.

She just laughed, because he was right. This was going to be a juicy night. "I'll see you at the office," she said as she locked the door behind her. She was actually surprised that waking up next to her partner wasn't as awkward as she thought it might be. She thought there might be some regrets but there wasn't a single one. She knew she made the right decision by telling Jay that they'd take it past partners and they'd figure out how to make it work. Would it be easy? No. But they would try.

When she walked in, there was nobody in except Voight. So she figured she might as well get it over with now. She walked in with both sheets of paper in her hand and closed the office door so if anyone did come in, they didn't hear.

"Is that your resignation letter?" Voight asked gruffly, from behind the desk.

Hailey wasn't sure if he knew about her and Jay or not. But she was going to string him along for a minute or two. "And if it is?"

Voight closed his eyes and leaned back in his chair. "Then I guess I'll let you have your first pick at your replacement."

She rolled her eyes. "Now I feel like I'm being pushed out the door already. But truly, I came by to give you these."

Voight took the papers and raised his eyebrows as soon as he realized it was not a resignation letter. It was HR forms. HR forms, stating that Hailey and Jay were co-workers in a relationship. CPD rules. "Really now?"

She shrugged as she started to make her way out of the office. "You told me to talk to him before I took the job."

"I guess I did."

"It won't affect the job."

He shook his head as he filed the papers in his desk drawer. "It better not," he threatened. He'd have a talk with Jay, similar to the one he gave him when he found out about him and Lindsay. This one would be a little different. "It becomes an issue, I will bounce you."

She smiled. "Good thing I have Chris Lynch with an open job offer, waiting for me if you do," she smirked as she walked out of the office.

* * *

Hailey was just finishing up her paperwork when Platt came up the stairs to tell her that she had a visitor. It was later, 8 pm, but Allie said she was still game for a quick bite to eat and then working out.

"Thanks Trudy. Tell her I'll be down in a minute." Hailey said as she locked her computer down and stood up. She remembered that Antonio had a gym that could be useful to her and Allie tonight and he was right beside her.

"Yo, Antonio. Can I borrow your gym later tonight?" He had a squat rack, benches, turf, and weights in the back of the actual boxing gym.

He looked up at her. "You know you do have a gym membership to two gyms," he pointed out. She had access to CPD gyms and also belonged to a franchise 24/7 gym.

She grimaced. "I know. Remember Allie Montgomery from Narcotics? She just came back from an 18 month undercover bid and well…"

"You need somewhere where there aren't people?" Antonio laughed. "I get it. Yeah, that's no problem at all. There's a lock box at the back of the gym. Code is 3480. I think Michael was finishing the last class up around now anyways so you'll have it to yourselves."

"Allie appreciates it," Hailey said as she quickly made down the stairs.

She was surprised to see her long time friend, who always had a shoulder length platinum blonde bob, with long dark, almost black hair. The green eyes were still the same and the unmistakable smile. "Look what the cat dragged outta the bag," Hailey said as she greeted Allie. "Sorry to make you come down here."

"It's good to see you. It's no problem. I sold my car before I went under, and honestly, all I've been doing for the past 5 days is sleeping and baking. If I've needed anything I've just used my mom's car. Guess I really should rent something or go buy."

"Did you have dinner?" Hailey asked, as she pushed the door open to the back lot. Normally she wouldn't let just anybody back through here but Allie was CPD.

Allie shrugged. "Not much."

Hailey unlocked her truck and both girls jumped in. "There's a guy who makes a mean sandwich not far from here," Hailey said. "He's also on the books as my CI if anyone asks."

Allie laughed. "Good to know. I also forgot, I don't have a gym membership. I guess we could go workout at a CPD gym," she said, hesitantly.

She signalled to pull out of the lot. "Yeah, I got you covered on that one. Antonio Dawson co-owns a boxing gym and they have some stuff in the back. Any secrets are completely off the record, not recorded and will not be heard past those walls."

"Knew I could count on you," Allie said, appreciatively. Truthfully, she had no idea who she could reach out to once she was back. 18 months was a long time to be gone and while cops understood it was part of the job, Allie didn't have a lot of department friends. But the one friend she did have, never judged her and was always there for her, no matter how long it had been.

They had grabbed the sandwich, which Allie raved about and Hailey said she'd pass the good reviews along to her CI, and then headed for the gym. Allie gradually let loose about a lot of things that she could share to Hailey. It was a hard undercover op, even for a seasoned veteran like Allie, and she was rattled by it and having a hard time. That's why it was important to have friends like each other.

They were also kicking each other's asses in the gym. "One more!" Allie encouraged as Hailey did one more rep.

She put the bar down and shook her head. "Fuck, you got in shape when you went under," she said. And then her phone rang, cutting through the music that was playing. Allie looked at her. "And that's also my you can't ignore this phone call ringtone." She pushed pause on the music and answered the phone. "I have plans."

It was Ruzek. "I did too. Voight just called. Two bodies down by the pier."

"Fuck," Hailey said. "I'll be there, whenever."

Allie turned to her and laughed. "You know crime doesn't sleep." It was nearing 11:30.

Hailey rolled her eyes. "I'm sorry. I can drop you off at your mom's or… you can be a real cop like the rest of us and work a case?"

The brunette laughed really hard at that one, but just shrugged in agreement. "Ah sure, what the hell. Haven't worked a real homicide case in over 3 years but why the fuck not. Good thing I brought my badge when I met up with you."

Hailey's phone rang again, this time it was Jay. "Ruzek already called," she said as a greeting.

"You still with Allie?"

"Yeah."

"Where are you guys?"

Allie was starting to put stuff away and Hailey was gathering their things. "At Antonio's gym. We'll meet you there at the pier."

"We'll?" Jay asked. Leave it to him to catch that.

"Easier to ask for forgiveness that permission," Hailey said. "See you there."

They got to the pier and Hailey looked over at her friend and Allie just shrugged as she got out of the truck. To any passer by, she sure didn't look like she belonged at the crime scene. Allie wore black leggings, converse shoes, and an oversized under armour hoodie, her dark brown hair in waves and heavy makeup on. She could totally pass as a co-ed. The only thing giving her away that she was a cop, was the Chicago PD badge hanging around her neck that hadn't been worn in awhile.

They got to the crime scene and Ruzek, Halstead and Voight were already standing there. Even Voight was confused on who this newcomer was. Halstead only knew it was Allie because Hailey told him that she was tagging along.

"Everyone, Detective Allie Montgomery," Hailey introduced.

Voight snickered. "Woulda walked right by you in the street."

Allie smiled. "Kinda the point of the change in looks, Sarge." She knew Voight from a couple cases from 3 years ago when she was permanently in Narcotics for a full year and not undercover.

"Officer Adam Ruzek and my partner Detective Jay Halstead," Hailey said, more for Adam's sake than anything.

They walked over to the bodies and Ruzek began the spiel. "Two both with two to the chest. IDs came back, Carl Williams and Martin Powell. I haven't found any gang affiliations yet but I haven't looked too hard."

Jay rubbed his hand. "I think these guys run with the G-Park Lords."

Hailey sighed. "Great. So we have to talk to Little Dougie? Where's fucking Rixton when you need him because Kenny's the only cop Little Dougie will talk to or at least cooperate with."

"He'll talk to me," Allie said softly.

All four Intelligence cops looked at the outsider. "Really?" Ruzek asked, doubtful.

She shrugged. "He has, at least in the past."

Voight sighed and held up a hand. "You're technically not back on duty so I'm not dragging you into this mess yet."

Jay knelt down beside the body and picked out a package out of Williams' pocket. It was cocaine, with a sticker on the outside. Somebody's signature. Hailey shone her phone flashlight on the sticker so they could all see.

"I don't recognize it," Halstead finally said.

Voight shrugged. "Can't say I have either but send it over to Carmichael over at Narcotics and see if one of his guys knows or has a CI who knows."

Allie rubbed her chin with her hand. "No need. I know who's it is."

Voight shone his own flashlight in her face. "Huh. Care to share Detective?"

She sighed and debated how much to tell them. "We'll you're not going to be knocking his door down tonight, I'll tell you that much. It's cocaine laced with something, most likely. The main dealer's name is Patrick Davis. This is probably one of his mid dealer's though."

"If I can't go kick down Patrick's door tonight, who can?" Halstead asked.

Allie shrugged. "You can visit him in a cell in a precinct in San Diego," she offered.

Voight rolled his eyes. "Well, all this is enlightening," he said sarcastically. "Clearly, I'm going to need to make some phone calls. Ruzek, you stay here until the M.E. gets here and in the mean time, see if you can't wake up some guys in Gangs and see if these guys really were G-Park Lords. You two, get some sleep," he told Upton and Halstead. He turned to Allie. "And you, don't leave town. I'm gonna need you tomorrow."

* * *

 **AN: Story it is. Really didn't plan on introducing an OC into here but I got started, and I'm rolling with it. If you guys have any plot suggestions for this story, shoot em over in a PM or review. More actual Upstead moments will happen next chapter but I'm also just letting the plot bunnies take me where they may...**


	3. Chapter 3

Jay, Hailey and Allie walked back to the two trucks and came up with their plan of attack. Jay looked at the time and grimaced, it was nearing 1:30 am. "It's getting late." He was tired, he knew Hailey was tired and he also knew that a good nights sleep was night going to come for the two of them on this case.

"Lets just all go back to my place, it's the closest and we can get an early start on the morning," Hailey suggested. She turned to Allie. "You cool with that? That way you don't have to wake your mom up or anything."

Allie nodded. "Something told me I should bring an extra pair of clothes with me in my gym bag."

Hailey turned to Jay. "Meet you at home."

Once Allie climbed into Hailey's truck did she look at her and laugh. "You're sleeping with your partner aren't you!?"

Hailey groaned. "It's been like a day, okay," Hailey said as she started driving.

"You're sleeping with your partner. The woman who swore she would never sleep with her partner, is sleeping with him," Allie exclaimed.

"You don't need to remind me," Hailey said. "It kind of just happened. I got a job offer and well, we kind of had to talk about us."

Allie smiled. "Good for you. He's smoking hot so good job."

Hailey rolled her eyes. "He comes with his own set of baggage but we'll see how things go."

They all got back to Hailey's pretty quickly and all brought gym bags inside with them. "Hey, do you have any tea or anything?" Allie asked when they got inside.

Hailey laughed. "There might be some in the corner but I don't know if it's any good. I'm a coffee girl, you know that. Bedroom is the on the right, there's an ensuite and there's towels in there if you want a shower. I'll probably be up around 7."

Allie smiled. "Thanks Hails," she said, as she went to go look for tea.

Jay was searching around in his gym bag that he had thrown on the floor when Hailey came into the bedroom. "What are you looking for?" she asked.

He held up the offending prescription pill bottle and made his way into the kitchen where Allie was waiting for hot water to boil. He threw her the pill bottle and she caught it. "Figured you might want one of these."

She read the label. "I sure as shit do. Thanks," she said as she popped the lid off, took it and dry swallowed the little pill and threw it back to Jay.

"Coming back is always the hardest," Jay said.

She sighed as she leaned against the counter. "I guess that's why I told Hails I would go with her to the crime scene. It's not my normal jam as far as being a cop but it sure beats sitting at home and baking."

Jay nodded. "I know that all too well. Anyways, I hope that helps you sleep. Night, Allie."

"Night."

* * *

Hailey woke up the next morning to Jay's alarm going off and she just laid there and didn't move.

"Turn it off," she muttered.

He reached for his phone and turned off the offending alarm. It was 6:30 and they had gotten to bed at 2:15 and they were both flat out exhausted. Neither of them felt like getting out of bed. He lazily put his arm around her.

"Do we have to go into work today?" she still hadn't moved from her position.

Jay just looked at her. "Voight will kill us, especially you, if we don't."

She rolled over onto her side so she could face him. "I'm exhausted, I don't want to deal with drugs, gangs and undercover ops. I want a day off. I just want to do nothing."

"So let's do nothing after this case is over," Jay said. "A complete day of nothing."

"You talk an excellent game Halstead," Hailey replied.

He looked at her. "Is Allie up and cooking breakfast?"

Hailey paused. "I think so. Which is really weird. Because she is the last person in the world to be cooking breakfast," she said. She dramatically threw off the covers and got out of bed. She was wearing one of Jay's huge gym shirts that covered enough of her ass that it was acceptable so she didn't bother putting anything else on.

Both Jay and Hailey made their way to the kitchen where Allie was making French toast for the three of them. "I've known you for over ten years and this is probably the first time ever you have ever made breakfast. Hell, even had breakfast."

Allie laughed. "Never was much of a breakfast eater in college."

Jay held up his hand. "Wait, you two lived with each other?!"

Hailey laughed as she started making coffee. "Yeah, for a semester. Allie, me, one of my brother's, and his friend. It was an interesting semester."

"Oh I want to hear the stories."

Allie flipped a piece of French toast. "Oh I got em."

"Can we get back to the fact that you are cooking in my kitchen, please?" Hailey asked as the coffee was done and she passed it to Jay before putting in one for herself.

Allie shrugged. "18 months changes a person."

* * *

Hailey and Allie ran up the stairs to find most of Intelligence, save for Jay, already seated at their desks. Atwater, Burgess and Antonio all looked very well rested and Ruzek looked like he hadn't gotten any sleep last night at all.

"Morning," Ruzek said, nodding at Hailey and Allie.

"Antonio," Allie greeted.

He did a double take at the new look on the Narcotics Detective, with her dark brown hair down again. "If Upton hadn't said that you were back in town, I would be seriously wondering who was standing beside me."

Hailey turned to Atwater and Burgess. "Officers Kevin Atwater and Kim Burgess. Meet Detective Allie Montgomery. She's being sucked into our latest case," Hailey explained.

Voight came out of his office at that moment. "Where are we on that, anyways?"'

Ruzek stood up and rubbed his eyes as Halstead come in. Hailey knew he had to make a stop for Platt before coming into the office. She didn't push. "Well I finally got a hold of Wilson in Gangs at like 3 or 4 in the morning. He did confirm that at least Williams is known to run with the G-Park Lords. Powell is still a unknown."

"But most likely is running in the same crew," Antonio said. "So who is picking the short straw to talk to the G-Park Lords?"

Allie raised her hand.

Voight shook his head. "Where are we on the drugs?"

"Cocaine. Cut with battery acid," Kim said, reading the report.

Voight, Hailey, Jay and Ruzek all turned to Allie and she threw her hands up in surrender. "New one to me. I was only the accountant. Voight, I'm sure you know what my role in that crew was."

"Yeah, woke up your handler last night. He was less than impressed that this got dragged out east and that his air tight case got a little bit more messy," Voight said. "I did remind him that if we nail these sons of bitches the right way, we might be able to put another nail in Patrick Davis' coffin."

Allie turned to Kim. "I am a little out of touch on how long things take these days but have fingerprints come back on the cocaine packet?"

Kim shook her head. "Not yet. I'll let you know. Is there someone we should be running them against?"

Voight just nodded. "I'll take care of that. In the mean time, we gotta play the G-Park angle here. Who wanted these kids dead?"

"Little Dougie has probably gone underground," Ruzek pointed out. "They are laying low if they know."

"What if the G-Park Lords don't know yet? Gangs said so themselves, they only have Williams on their radar. These guys probably aren't super tight in with the crew. It's only been a couple hours," Hailey said.

Halstead shrugged. "Could just surprise Little Dougie."

Voight quickly walked over to his office and walked back and handed a gun and a burner cell phone to Allie. "Welcome to Intelligence for a couple days," he said. "Don't do anything stupid. Upton and Montgomery, go pay Little Dougie a visit. If he won't cooperate, I will call Rixton but lets not go that route if we don't have to. Everyone else, start calling CIs on how cocaine from San Diego got to Chicago."

Allie took the gun and tucked it in the back of her black, slightly ripped jeans. She wore the converse shoes she wore yesterday, along with a pink zip up hoodie. Her Chicago PD badge hung around her neck. Her attire wasn't too different than Hailey's, who wore boot cut jeans and a blue plaid top. Hailey's badge was just on her hip, along with her gun in her holster. "I won't. You want me to play this on the drug or the gang angle, Sarge?"

"Gang," Voight said.

Kim handed them a piece of paper. "It may be 10 am but Gang always has surveillance on and he's parked outside his bar."

"Not surprising," Jay muttered.

Hailey and Allie got into the truck. "There's another hip holster in the glove box," Hailey said.

Allie shrugged. "Thanks but I'm good. Rather keep it on my back. I have a back holster in there right now. It was in my gym bag. Habit from always carrying in California."

"Concealed carry is against the law in California," Hailey commented.

Allie just looked at her. "I played the part of basically a criminal for 18 months. Didn't really care about that shit."

They talked about aimless stuff for the rest of the drive to the bar where the G-Park Lords occupied most of the time. They talked about their undergrad degrees, how Hailey had gotten her Masters but Allie went straight into the arms of the US Marines. They talked about Hailey's family and how her three brothers were doing. They talked about Allie's mom, her only family left, and how Gloria was doing now that Allie was back. And they talked about how much shit Ruzek looked that morning.

"Let's do this," Allie said as she headed for the bar; she took off her CPD badge and stuffed it in her pocket. "Let me go in first."

Nobody was at the front doors which surprised them both but they didn't draw their guns. Little Dougie was sitting at a table with his younger brother when the two of them approached. He didn't barely glance at them, or the fact that two white girls were walking into his bar at 10 am register with him.

"It's been a little awhile!" Allie exclaimed.

"It's been awhile," Hailey echoed. She was always amazed at her friend's ability to change identities and personas on the fly. She was a natural born undercover operator.

Little Dougie was so confused. "Who are you two?"'

Allie turned to Hailey. "He doesn't remember us? Seriously?" Hailey just shrugged.

"I don't remember. Leave," Little Dougie replied.

And then Allie's face turned and she slammed her CPD badge on the table, surprising the G-Park Lords leader. "Nice try. You know me. I just look a little different. Detective Allie Montgomery," she said, jogging his memory. She pointed to Hailey. "Detective Hailey Upton."

Little Dougie looked at Hailey, who simply crossed her arms. "It's been awhile."

Allie sat down at the table across from him. "I need information."

"What kind of information?"

Hailey held out her phone and flipped between the photos of the two dead gang bangers. "Two of your guys are dead."

Little Dougie just looked at his brother and then back at two female Detectives. "What happened?'

"Took two to the chest last night down at the pier," Allie raised an eyebrow. "Losing touch? Because I'm surprised you haven't heard that two of your guys are dead."

"Been a little busy," Little Dougie said.

Hailey smirked. "Shame."

"What do you ladies really want?"

Allie sighed. "Your gang bangers were found with cocaine on them. Know anything about that?" She showed him the picture of the cocaine package.

Little Dougie shook his head, emphatically. "I tell my guys to deal with one dealer that I trust and not to go outside of him."

"Looks like they did," Hailey said. "We need your help."

"We won't go after you guys for your cocaine, we could care less about that at this point," Allie said. She did make a mental note to figure out who the G-Park Lords were using as their main dealer. "But we need you to help us find out who sold that cocaine to Williams and Powell."

Little Dougie seemed to consider the proposition. "Yeah, okay. I can do that. I'm meeting Rixton tomorrow."

Allie looked at Hailey who just rolled her eyes. Instead she grabbed a bar napkin and a pen from the table and wrote her number down. "How about you call me? You don't want to turn to the chance to spend some quality time with two pretty Detectives do you?"

This time Little Dougie rolled his eyes. "Yeah, yeah. Get lost. I'll call you or Rixton."

* * *

 **AN: Thoughts?**


	4. Chapter 4

**AN: You get two chapters this week anddddd its primarily a Upstead chapter. So if you like it, leave me a review!**

* * *

At the end of the day, Voight told them all to go home. They weren't going to get far without Little Dougie and Allie's handler's cooperation and at that point, they had neither. They had given Rixton the heads up that Little Dougie might go through him to give the information regarding Williams and Powell. Ruzek lived close to Allie's mom's house so he drove her home.

Jay and Hailey were the last to leave, even after Voight. "Pizza?" Jay asked.

She leaned back in her chair and sighed. "I guess. I sure don't feel like cooking. It's your turn for your pizza."

He flashed his mega-watt smile. "I know."

She rolled her eyes. "So that's why you want it?"

He shrugged as he picked up his jacket. "Maybe."

"Fine. But you text him and deal with him. He is your CI," she pointed out. His favorite pizza store was run by a bunch of drug dealers and they usually texted their orders in to avoid being seen in that pizza store but Jay couldn't resist it.

"Small price to pay for Chicago's best pizza," he said as they made their way down the stairs.

They split up as they made their way to the parking lot. "See you at home."

She was washing dishes when he came in the door with beer and two pizza's. One being for her and the other for him. They had much different taste in pizza they learned, being partners so they knew it was always best just to order two separate pizzas and have the rest for leftovers. This wasn't the first time they had ordered pizza, they usually did it on their sports nights or before going to Molly's.

"I bought you your favorite beer," Jay said as he set the pizza and beer on the counter.

She turned around from the sink and raised an eyebrow at him. "Nice try. Because you know I drink what you drink."

He shrugged. "It was worth a try."

"A better one would be buying me cheesecake or something," she said as she grabbed two plates.

He opened the pizza box. "I'll save that for when I fuck up and I need to get on your good side."

"You do that."

They made their way to the couch and Jay took the remote. "What are we watching tonight?"

She shrugged as she took a bite of her pizza. He turned it to a Blackhawks game and she didn't complain either. They were in Florida tonight, playing the Panthers and by the score, they were well on their way to getting their asses handed to them, as the Panthers were up 4-0, 6:12 into the first.

"This is embarrassing," Hailey said, about the score.

Jay shook his head. "No shit. I don't think there is anything else on, unless you want to turn on Netflix."

"And aimlessly go through Netflix trying to decide what to watch? No thanks. Let's just watch this."

They had finished their pizza and put it on the coffee table and she was cuddled into Jay's side. She thought about how weird it was that three days ago they were just partners and now they had moved into a different type of relationship and it just felt so natural. It felt so right that he should be at her place after some rough couple days, eating pizza and just trying to rest as much for the next day.

For Jay, it was about time that they had moved their relationship into something else. They had been dancing around their under lying feelings for along time but neither of them knew how to move on it or if they should. Being partners at work and being in a relationship was a huge step and both of them knew they had to be fully committed to making it work if they made the plunge. He had done it before with Lindsay and it did make him a little nervous to be involved with another partner. He also knew what would be said about him at the district but he didn't really care. Hailey was worth it.

The Blackhawks game was almost over before Jay turned to Hailey. "Did Allie serve?"

"That's a random question, but yeah."

Jay nodded. "I got that feeling when she said something about having a hard time coming back. She deploy?"

Hailey pulled up a picture on her phone and showed him. "Did 4 years and got out as a Captain."

Jay whistled. "Too bad she's a Marine but wow she rocks that uniform." He may be head over heels for the girl sitting next to him on the couch but he couldn't deny the hotness of a young blonde Captain in uniform, holding a gun with the Iraq background behind her.

"Pretty hot, eh?"

He nodded. "How come she got out? She seems like she would go far in the military."

She shrugged, debating how much to tell him. "Allie got raped her junior year in University and ran straight into the arms of the U.S. Marines. Her high school sweetheart had enlisted and was doing really well and they were talking again so she decided that it was the best thing for her. The Marines were never her real long game. When it came time to re-up she was feeling restless and following orders isn't something Allie is very good with."

Jay whistled. "Wow, that's a seriously fucked up past."

"She somehow did OCS in between her junior and senior year while everyone, including me, was partying their ass off or doing nothing. She came back her senior year, completely changed. I don't know if it was the rape or if it was the Marines that broke her and changed her but after that, her ability to change and become a different person was amazing."

He was starting to realize there was so much more to Hailey's friend that the façade she put on. "It's her way of coping."

Hailey nodded. "She joined CPD right after getting out of the Marines and she could go out partying all night long and she did quite often and come back like nothing had happened the next day."

"I did it too," Jay said.

"I know," Hailey said, softly. "You two deal with anger and disappointment and your past a lot in the same ways."

He smiled softly. "So that's where you got so good at dealing with me when I start to go down the rabbit hole."

She nodded. "I've had a little bit of practice with Allie. Don't let her fool you too much. She might be all buttoned up 99% of the time but I've seen that 1% and it's not pretty."

"Neither is mine."

Hailey took his hand and looked him in the eye. "I know. And I'm fully prepared for that 1% and will love you even through that ugly part."

All Jay could do was kiss her and she giggle so he kissed her more and soon he was on top of her on the couch. Yep, he was head over heels for his partner.

* * *

It was 1 am and Ruzek was with a woman in an upscale bar, far from any co-workers. Her name was Melissa and she was not the normal girl he dated. And she did not know he was a cop. And he didn't want to tell her either. They were together the night Voight called him and she was less than impressed when he had to go. He had met her through another friend but he knew it was probably nothing if he couldn't even tell her he was a cop.

His cell phone started vibrating in his pocket. The number wasn't saved in his phone but he recognized the digits as some of the burner phones Voight had gotten for them to call their CIs with. So it was coming from a CPD cell phone. "Hey, I need to answer this."

She looked at him disapprovingly but he still stepped outside the bar on the smoking patio to answer the call. 'Hello?"

"Can you come pick me up?"

Ruzek had to steady himself on the railing he was so surprised at the voice on the other side of the call. It was Upton's friend, Allie Montgomery. And she sounded wasted. "Allie?"

"Just come fucking pick me up please," Allie pleaded.

Ruzek looked inside and sighed. He knew she must be pretty drunk for her to be calling him. Normally he'd tell his friends to go get an uber or taxi in a case like this but his gut was telling him that he better pick her ass up. "Where are you?"

"Bar in G-Park Lord territory. I'll drop you the pin," she said.

Now he really wanted to kill her. She was a white, female cop in the wrong side of town and that was just asking for trouble. "Fucking stay there Allie. I'm coming right now."

"Yeah, yeah, yeah," she said and he hung up the phone.

He walked inside and Melissa was already gone. He just rolled his eyes, probably for the best. If she couldn't handle a couple 1 am phone calls, then it was definitely doomed. He paid for the tab and got in his vehicle. G-Park Lord territory was pretty far from where he was but he got there pretty quickly.

When he got there, Allie was sitting at the bar, talking to the bartender that Ruzek recognized as one of Atwater's CI's.

The bartender nodded at Ruzek and they stepped to the side. "She's already paid her tab but she's pretty messed up. Given the fact that you're here to pick her up and the wide berth everyone else gave her in this bar, I'm guessing she's a cop?"

Ruzek nodded. "Yeah man. Thanks for keeping an eye on her."

"You came," Allie said, when she saw him.

He shook his head. "Come on, lets go. You are wasted, my friend."

She slowly stood up. "I know."

He put his arm around her waist to steady her as they started to walk out of the bar. "So what happened?"

"Life fucking happened."

He didn't say much in the car and she didn't either. He debated whether to drive her home or let her sleep it off on his couch. He elected that letting her sleep it off on his couch was probably a better idea, given that she was staying with her mom and he still was going to pick her up in the morning anyways.

Before they got to his place, he asked the burning question. "Why'd you call me and not Upton?"

She waved her hand. "Hails has dealt enough with me like this and you seemed like you would know the best out of everyone else on what to do and how to deal with a very fucked up me."

"Thanks for the sort of compliment," he said softly as he helped her get out of his car.

* * *

It was 3 am and Jay's burner phone started ringing. It was the cell phone he had that he dealt with CIs with. He rolled over and saw the name of his CI- Devante Mayfield on his caller ID. This better be huge for Devante to be calling at 3 am and waking him up. He hadn't had many dealings with Devante lately- he was running with a new crew and trying to move up the ladder there. He was friends with a lot of the G-Park Lords but never officially ran with them.

"Yeah," he answered.

"I think I know who killed Carl Williams and Martin Powell," Devante said.

Jay sat up in bed; that definitely woke him up. "What?"

"You heard me," Devante said.

Hailey was stirring beside him. "Meet me at the all night diner on 21st in 30 minutes'," Jay said. He was already throwing on a t-shirt.

"Yeah, sounds good.," Devante said and hung up.

Hailey rubbed her eyes. "What's going on?"

"Get up. We gotta go talk to Devante," he said.

She threw herself back on the pillow dramatically and looked at her phone. "It's 3 am."

He just looked at her. "Yep. Get up."

She groaned but sat up and leaned over to grab her jeans and put them on, but not without Jay looking at her ass as she was putting up her jeans. She just turned around and glared at him, which made him laugh, after she did her jeans up. She made her way into her closet in the dark and grabbed a t-shirt and threw a University of Chicago hoodie overtop of it.

Jay was in the kitchen, making them coffee. He handed her a coffee mug and she took it and kissed him in appreciation. He just laughed and put his own coffee cup in the Keurig.

"Do you think he actually has solid information?" Hailey asked.

He shrugged. "Too big of a case not to try."

"It's 3 am though," she whined.

They got to the diner where Devante was waiting outside, with his hands in his pockets. He raised his head when he saw the Duramax approach. "You brought the pretty lady," he said when he saw Hailey.

Jay and Hailey rolled their eyes. "Pretty lady will kick your ass if you don't start talking soon," she said as she opened the door.

They found a booth and the waitress brought them all coffee immediately. Jay and Hailey knew they were up for the long run at this point. They also took menus from the waitress.

"You can order you know," Jay said.

Devante shook his head. "I'm only here for a minute. I don't want anyone to see me."

Both cops respected that. That's why they were up at 3 am, meeting him at an all night diner. "Start talking then," Jay said, looking at the menu, knowing he wanted their strawberry pancakes. He knew Hailey would order the same most likely.

"I think Carl Williams' dad killed him and Powell," Devante said, leaving the two Intelligence Detectives absolutely and utterly shocked.


	5. Chapter 5

**AN: Short chapter for your lovely Black Friday!**

 **Also, this chapter does have a little bit more swearing that normal. I try to make my stories somewhat as realistic as possible and my cop/military friends definitely do not have saintly mouths in real life and in the work place (nor do I)**

Jay and Hailey just looked at each other and then back at Devante. Did they just hear that correctly? Carl Williams' own dad killed him? That was pretty unheard of, even in their line of work. "Wait, his own dad killed him and his best friend? Did I hear that correctly?" Jay asked.

Devante shrugged. "Yep."

The waitress interrupted their conversation. Jay ordered pancakes with strawberries on them, Hailey ordered waffles with strawberries on them and bacon on the side. Jay just rolled his eyes at the added bacon part leave it to her. She ordered bacon on the side with every breakfast meal she had. It was a thing she had. Jay didn't understand it. He would just be concerned the day she didn't order a side of bacon.

The waitress left and Hailey raised an eyebrow towards Devante. "Where'd you hear that from?"

"You know that Williams' cousin, Keisha, and I are tight," Devante said. "She told me. But you didn't hear that from me."

Jay nodded. "Okay. Why? Why would Carl Williams' dad whack his own kid?"

"Something to do with dealers. G-Park Lords are supposed to deal with one dealer only," Devante said.

"Spike," Hailey interrupted.

"Williams' dad and Spike are in super deep on something. Carl's dad found out that Carl started dealing for some guy out of San Diego. And he was super pissed because Carl was dating some chick from Southside," Devante explained.

Jay shook his head. "And Powell was collateral damage. That's fucked."

Devante sighed. "That's why I told ya'll. Anyways, I fucking gotta get outta here before anyone fucking sees me."

Both Jay and Hailey nodded at him. "We'll be in touch," Jay promised.

The waitress came by shortly with their food, which they were forever grateful for so Jay decided to ask the question that had been on the back of his mind for awhile. "When are you going to turn down Chris Lynch?"

Hailey took a bite and then pondered. "I have a week to think about it. I already texted him asking to meet, if that's what you're wondering."

He shrugged. "I was just wondering."

She rolled her eyes. "I made up my mind that night. You know that."

Jay was reading her mind already. "You're going to pitch Allie going."

And then everything went to hell. Bullets started flying from an automatic machine gun and Hailey and Jay took cover in the booth they were in. They noticed it was a drive-by; a dark sedan. The shooting didn't stop until all the glass in the front was destroyed. Hailey looked to the back and saw the waitress crouching behind the kitchen; she was safe there. Thankfully there was no other patrons in the restaurant at the time, it was just the two cops.

As soon they felt it was remotely safe enough, Hailey and Jay ran after the vehicle that was involved in the drive by. Hailey managed to get one shot off, into a black SUV. Normally she would never take a shot in the street like that, but it was 3 am.

"Shots fired at plain clothed officers, corner of 21st, Peters All Night Diner," Jay told Dispatch as they started into the distance. "Fuck," he swore. More about the fact that he couldn't get the shot off cleanly or the fact that two officers basically just got ambushed at an all night diner at 3 am. He really wasn't sure what he was more mad about at this point- probably the latter. He hated getting shot at. Especially without a vest on.

And then he turned around and saw that Hailey had been grazed by a bullet in her shoulder. Great. Even better. "Officer shot. I need an ambo down here for sure," he said to Dispatch.

"Already got one coming."

Hailey didn't look scared, nervous or concerned about the fact that blood was running down the side of her arm. Instead Jay just held it his hand there to stop the bleeding. "My turn to get shot," she said, sarcastically.

He rolled his eyes, as he watched his hand get covered in blood. "Funny one you are. I suppose we should really call Voight now."

She tried to shrug. "I still think we wait until a more appropriate time of the morning."

"You were just shot!"

She glared at him harder. "We compromise and call Antonio."

Jay seemed to consider it. "He would figure things out between us two."

She rolled her eyes. "Bound to happen anyways. How about we flip for it? Heads, Voight. Tails, Antonio."

"Deal," Jay said, as he got a coin out of his pocket. It landed on tails so Antonio it was.

"Yo, Antonio."

"This better be good for 3:45 in the morning," Antonio said when he picked up his phone.

"Is Hailey just got shot and we figured out who killed Carl Williams and Martin Powell considered good?" Jay was just being an ass at this point but considering Hailey didn't seem to be in too much pain, he thought he could have some fun with this.

That woke Antonio up. "Hailey just got shot!? What the fuck!?"

"Relax, bro. I think she's fine. Dispatch said an ambo's coming," Jay laughed. "Just wanted to get you out of bed super fast."

"And you accomplished that. Where are you guys?"

"Peters All Night Diner on 21st."

"See you soon. Don't get shot again."

The ambulance showed up and soon uniforms showed up. Uniforms went to go take the waitress and cooks statements. Someone from Intelligence would take them again but they wanted to get their statements ASAP. Hailey was in the back of the ambulance getting looked at the paramedic when Antonio showed up. He rolled his eyes as he walked forward. "Your turn, eh?"

She tried to shrug. "Guess so."

"So why are you two together at this ungodly time of the morning?"

Jay and Hailey looked at each other. "I wasn't about to go meet my CI alone, 3 am or not."

"So you woke her up," Antonio said, pointing between the two of them.

"Would you I rather have woken you up?" Jay fired back.

The older Detective shook his head. "Fuck no. Why'd Devante call you that early anyways?"

"Knew who killed Williams and Powell and didn't want to be seen with us," Hailey said.

"So who killed them?"

Jay bit his lip. "Here's the kicker. Devante was told it was Williams' own dad."

Antonio whistled. "Alright. Is it a solid theory?"

"Yeah, might be a little hard to prove. Basically he wasn't dealing with Spike, who he should have been dealing with, and went to go deal with a new guy from San Diego. Allie's connection to the case," Hailey explained.

Antonio sighed. "That's gonna be hard to prove."

"It is. Still don't know the how or the why on how Williams got in with some moron drug dealers from San Diego who cut cocaine with battery acid but it's a start."

The paramedic looked at Hailey. "I still think you're gonna need to go to the hospital and get this stitched up."

Jay rolled his eyes. "Fine. Let's go. I think my brother's even working tonight. He'll be thrilled to see you."

She looked at Antonio. "Great. A Halstead reunion at 4 in the morning. How lovely for me."

In the end, they ended up going to the hospital. Thankfully not in an ambulance but Halstead drove them to Med. Hailey was not enthusiastic about the possibility of getting stitched up without freezing, as she was allergic to lidocaine. Leave it to her to have an allergic reaction to medications that people shouldn't have allergic reactions to. She was not impressed about this whole situation.

Will sleepily rubbed his eyes as he came inside the room that Jay and Hailey were waiting in. Hailey was on the bed, hand still pressed against the bleeding gauze and Jay was sitting in a chair. "I was actually asleep," he whined.

"And I just got shot at," Jay said.

"And I was actually shot," Hailey retorted.

Will just rolled his eyes and looked at Hailey. "Good to see you again, Hailey. Natalie's been asking about you. More in terms of, 'what's going on with that pretty partner of Jay's?'"

Hailey shot a look at Jay. "Oh has she been? I guess I'll have to shoot her a text or something."

Will put up his hand. "Hold on. Did something change between you two?"

Jay rolled his eyes at his brother. "Don't worry about it. Just fix her please. Don't use lidocaine on her though."

The doctor took off the bandages the paramedic had applied and whistled and then looked at the blonde Detective. "Are you allergic to lidocaine?"

"Lidocaine and morphine," Hailey said. "Don't ask."

He pointed to Jay. "And he knows this."

"He also knows my blood type. It's his job," Hailey said. "I know his as well."

Will seemed to accept that point. "This is going to leave a nasty scar. Sorry. Dr. Choi is a little better at suturing actually but he's not on shift."

"I'll just get a badass tattoo to cover it anyways," Hailey joked.

Jay laughed. "Just what I wanted in a girlfriend. Blonde hair, blue eyes and lot of tats."

Will just looked at the two of them. "I don't even know about you guys," he said as he began to gather the supplies needed to suture Hailey's wound.

"It's fun," Hailey said.

Will started to get serious. "This is about to hurt. Really hurt, especially without freezing. I can do it with Marcaine or I can do it without, your choice. Do you know if you have allergic reactions to Marcaine?"

She shook her head. "Fuck it, stitch it without freezing,"

The doctor shook his head as well. "Chicago's finest, ladies and gentlemen. Jay, hold her hand. Hailey, squeeze his hand as hard as you possibly can. Don't scream, it will scare other patients. You ready?"

Jay gave Hailey his hand and she nodded. "Go ahead."

Will started suturing the wound. And more stitches got added. Every time he went through a layer of skin, Hailey's grip on Jay's hand tightened but her face to the outside word remained the same. Jay could tell that the pain was excruciating but her face still remained in neutral. In total, she ended up with a lot more stitches than Will or Hailey was expecting. So it was probably a good thing that Jay dragged her to the hospital.

"All done," Will said, finishing the last stitch.

Hailey let out a sigh of relief. "Can we never do that again?"

Jay snickered. "Right. If I remember correctly, you were just the one to say no to the Marcaine."

"Try and not get it wet for a couple days, which is obviously easier said that done," Will said.

"Does this mean I get to give you sponge baths?" Jay asked.

"I'm not going to even dignify that with a response," Hailey fired back.

Will shook his head. "I did not need to hear that, Jay. How did you guys remain partners for so long and now just change your relationship status on Facebook? I really want to know."

Jay shrugged. "Probably the million dollar question. It's not common knowledge though, so keep it on the down low."

Will narrowed his eyes. "Ya'll think you can keep it on the DL with how you were acting in here? Good luck!"

"We are highly trained Detectives who have done multiple undercover assignments," Hailey pointed out.

He shook his head. "You two are insufferable. Seriously. Nat is going to love this."

And then the mood shifted when Sergeant Hank Voight appeared in the doorway. Jay checked the time on his alarm. 4:32 a.m.

"So, you think you can get shot and not fucking tell me?"


	6. Chapter 6

Hailey crossed her arms and tried to hide the wince that came as the stitches stretched when she did that. She was still sitting in the bed, back against the bed as she watched her very angry boss come into the picture. Damn it all to hell, her shoulder really hurt now. Why did she refuse Marcaine? She was really stupid. "Yeah. It's 4:30 in the morning. We had things under control."

"And getting shot is having things under control?" Voight leaned against the door fame.

"I don't think things would have changed if you were at that CI meet at the diner, if that's what you are insinuating. We still don't know who's responsible for the shooting at this point anyways!" She started to raise her voice but Jay just gave her a look that told her to shut up.

"We flipped a coin after the shooting. Heads, you. Tails, Antonio," Jay explained.

Voight rolled his eyes. "A coin? Really?"

Hailey tried to shrug and also tried to hide the wince. The pain was really coming now. "Did you want us to call you at 3:02 when Devante called Jay?"

"No. But I sure would have appreciated a phone call from either of you instead of getting woken up by Howley because there was an officer involved shooting. My two officers!"

Will was still in the room and could see the winces that Hailey was trying to hide. He took a needle and filled it with Toradol and injected it into her arm and then gave her two painkillers. "It's Tylenol." She took it with the water that he gave her.

Jay, Voight and Will all exchanged a look. Will just managed to pull one over on Hailey. Jay fully expected that Will just gave her narcotics, which would bench her for a full 24 hours, minimum. He wasn't thrilled about that because that meant he didn't have a partner, but his brother had a point in what he just did. Hailey shouldn't be working. Voight or Jay telling her to stop wouldn't stop her, but she was a stickler for the rules, and would obey a CPD narcotic rule and not got into the field.

"We made a judgement call. We were going to call you when the time as a little more appropriate and not the middle of the night," Jay explained again.

Voight shook his head. "Both of your judgements need a little work. I'm going to go to the crime scene that I wasn't originally called to. You guys need to wake some people up," Voight said.

Will finally decided to say what he really gave Hailey, so her boss knew. "Oh and Voight, think you should know that it wasn't Tylenol I gave her. It was Oxycodone."

Voight just nodded at him and left.

Hailey however turned to him and glared at him. "Fuck you, Will. You know what this means."

"I sure do. You're benched for 24 hours. I did it on purpose because the adrenaline is wearing off and now the pain really starts. And you shouldn't be working. I know you wouldn't anyways but now you can't," he said as he left before she could argue farther.

Jay just took her hand. "He has a method to his madness."

"I'm not disagreeing with that, but I don't appreciate him pulling one fucking over on me," Hailey said, dramatically leaning against the back of the bed.

April came into the room. "I don't even have discharge papers because you weren't even admitted but," she handed a piece of paper to Hailey. "Antibiotic prescription. Just in case of an infection."

Jay nodded at the nurse. "I'll make sure she fills it," Jay promised. April nodded and left the room. He sighed and turned back to Hailey. "Let's get out of here."

She nodded. "I'll call Ruzek and Allie. You call Kim and Atwater."

They were in the truck and she dialed Ruzek's number from memory and put it on speaker. "Wake up," she said when he answered.

"Why are you calling so early?" Ruzek complained. "It's not even 5." He hated to hear her voice, considering he didn't go to bed until well after 1, after picking up Allie and making sure she was okay in his spare room.

"And I've been up for 2 hours already," Hailey said. "And shot. So get up, we have some work to do."

She could hear some moving in the background. "You were shot!? Christ, Hailey."

"Can you pick up Allie too? I'll call her."

"No need. She's at my place."

Jay and Hailed shared a look. "What do you mean at your place, Adam?!"

"Passed out drunk in my spare room," he quickly explained. He did not want Hailey to think Allie was in his bed, because she most definitely wasn't. "I'll explain later."

"Oh I want every detail," Hailey said before ending the call.

Ruzek got out of bed and threw some acceptable work clothes before going into the spare room to wake Allie up. She was still in the same position that he left her in last night. "Wake up sleepy head," he said as he gently touched her. Given her volatile state last night, he didn't want to alarm her too much. He had no idea what type of person she would be in the morning and he hoped to God she was going to be easy to wake up.

She opened her eyes. "Three words. What the fuck."

Adam crossed his arms as she tried to sit up and figure out what the heck was happening. "That was actually five words."

"Where am I?"

He shook his head. "You blacked out?" He didn't think she was that drunk, but apparently she was.

"Clearly. So help me out please."

"You called me at 1 am. You were at Winston's. Which is the absolute last bar to be in but the bartender is on our payroll so he made sure you were safe," he explained. "Your turn."

She sat up and pushed her hair out of her eyes. "Last thing I remember is leaving my ex-husband's place," she said.

That definitely surprised Ruzek. "We gotta go. Halstead and Upton ended up in a little bit of a situation."

She checked her phone, saw the texts and saw the time and just groaned. "Lots of coffee today," she said as she stood up and followed him out of the room.

He first dug around in a bag by his door and threw her a breathalyser. "Might wanna blow first. Don't mind how dirty that sounded." He was not going to let her come to work if she was about to blow over the legal limit to drive. He did not need a drunk cop on the job, and neither did Voight or Hailey. Although he suspected she had done the whole go out and party all night long and show up the next morning like nothing had happened song and dance routine.

"What are you doing with a breathalyzer at home?" Allie asked, as she looked at it.

He shrugged. "Blow."

She did and the numbers came back at him. "Below the legal limit. You're okay. Which surprises the hell out of me," he said, as he put shoes on.

She shrugged. "Can we stop by my place so it doesn't look like I was on an all night bender? Less than 5 minutes, I promise."

"Probably a good idea."

True to her word, less than 5 minutes, she came out of the house again in different clothes and a gym bag with makeup in it and applied the makeup as he was driving so it didn't look like she had been up pretty much all night. Thankfully he also stopped for coffee because she really needed one. And she needed Red Bull.

* * *

Jay and Allie were on their way to visit Little Dougie at his home to see if he was behind the drive-by shooting. They doubted it, but they had to cover all their bases. Jay hated dealing with gangs but he knew he had to take Hailey's spot today. Where was Rixton when you needed him?

"So, Ruzek?" Jay asked when they were pretty close to Little Dougie's house.

Allie shot him a look. "Nothing happened with Ruzek."

"Uh-huh," Jay replied, keeping his eyes on the road.

She shook her head. "Spare room and all my clothes on, thank you very much."

"Why'd you call Ruzek and not Hails?"

She shrugged. "I was drunk."

Jay accepted this as a reasonable answer as he signaled down the right street. Allie reached for her gun in her back and made sure it was fully loaded. She tucked it back in her waist. She did not want any surprises. And this wasn't her gun. It was a gun that Voight gave her.

They exited the truck at the same time and Jay pounded on the front door. They had waited until a somewhat reasonable time in the morning to pay them a little visit- 7 30 a.m. Allie was in favour of hitting it at 5 am, Voight and Antonio wanted to wait until later. "Little Dougie!" Jay shouted.

"It's Allie," she shouted. "You better open up!"

The door opened up. It wasn't Little Dougie. It was his younger brother, Curtis. "What ya'll fucking want?"

Allie pushed the door opened and walked right in. Jay had no choice but to follow her in. "Where's your brother?"

Curtis shrugged. "Not here."

"Yeah, I'll see about that," Jay said. He searched the house. No Little Dougie. He'd have to talk to Gangs about their 'surveillance.'

However, they did have his number two right in front of him. "You or your brother order the drive by?" Jay asked.

"What drive by?"

"Don't play dumb Curtis," Allie snapped. "I am not in the mood to deal with stupid this morning."

Curtis looked fidgety but Allie nor Jay could take him in based on him being fidgety. "I don't know anything about any drive by."

Allie had had enough. She pushed, or pretty much threw, Curtis into the wall behind him and stepped back after she heard him connect with the wall. Jay just gave her a look and she just shrugged back. "I told you that I don't want to deal with stupid today. Last chance."

"Last chance before what?" now Curtis was looking a little afraid, as he should.

She pointed at Jay. "Last chance before he lets me do what I really want."

Jay shrugged at Curtis. "She's just warming up. And she's right. I'm the reason you're not seriously hurting yet."

Curtis rolled his eyes. "Okay, okay. We heard about it. We didn't order it."

"But," Allie said.

"Spike."

Allie and Jay looked at each other and then back at Curtis. "Is Spike behind all this? Is he tying up loose ends?"

Curtis shrugged. 'I truly don't know. Little Dougie doesn't know either. He was also trying to find out what you guys asked him to do."

"Find out who Williams and Powell got the cocaine from in San Diego," Allie repeated from the other day.

Curtis nodded. "Yeah, something like that."

Jay knew that was all they were going to get out of the number 2 of G-Park Lords. Funny how the number 2 of a very well respected gang folded as soon as a female cop threw him around a little bit. "Tell your brother we stopped by."

* * *

Meanwhile, Hailey was still at 21st. She was sporting the sling that April had given her while they were walking out and a stern glare from the nurse told her that she should probably follow orders for a day or two. And then her phone beeped. DEA Agent Chris Lynch wanted to meet in 30 minutes. Problem- Hailey couldn't drive. However, there was another person there. And Atwater didn't usually ask too many questions.

Hailey stood up and went into Voight's office. "You mind if I borrow Atwater for a bit?"

Voight nodded at the phone in Hailey's hand. "Lynch?"

She nodded. "Yeah. I can't drive."

"Yeah, sure."

Hailey sat down on Atwater's desk, prompting him to look up. "We need to go. You're driving my pretty little ass around today."

He looked at her and then looked at Voight and back at her. "Alrighty, then. Where to?"

She looked at him as they went down the stairs. "Starbucks and then Grant Park."

Atwater stopped at Starbucks for her but it wasn't the coffee drink that got Hailey's attention. It was who was making the drinks in the drive thru that piqued her attention. It was her sister-in-law, Hannah. Someone who wouldn't or shouldn't be working at Starbucks because she was a stay at home mom to three kids, or so Hailey thought. Definitely got her interest going and Hailey was going to have to do some digging around later.

"You look like you saw a ghost," Atwater commented.

Hailey debated whether to tell him what she saw in there but decided the truth was the best option. "Yeah, my sister in law is apparently Starbucks' new barista there."

Kevin nodded. "And I'm guessing that is news to you," he said.

"It is."

For the rest of the ride to Grant Park, Hailey and Atwater talked about the most randomest topics, from the Chicago Blackhawks to whether Friends should do a re-boot. Once they got to Grant Park, Hailey had a bad gut feeling. She turned to him. "I have a bad feeling about this."

"Who are you meeting?" He was suddenly concerned.

Hailey debated whether to tell him, yet again, but Atwater was smart and he'd put the pieces together. "DEA Agent Chris Lynch. I don't have a bad feeling about him but I have a bad feeling about all of this."

Kev got what she was getting at. No staying in the car until she was done. "I'll be around."

She nodded as she got out of the vehicle but checked her firearm before she got out. She had her jacket covering it as the general public and the Ivory Tower would not like the idea of an injured cop in a sling having her gun on her. However, there was no way that she nor Voight would be okay without her gun not being on her if she had her badge on her. She completely was aware of her surroundings as she stepped out and noticed Lynch by a water fountain so she walked up to him.

"Wonder woman got a bullet hole in her," Lynch said as she approached.

God, was he an ass. "Wonder Woman got shot at before 4 a.m., thank you very much."

"Any suspects on that?" Lynch asked.

She looked at him. "Even if we did, I wouldn't be telling you."

"So, you taking the job or not?"

She shook her head. "But I think you already knew that."

"Had a feeling. Why'd you meet me down here then? You could have told me this over the phone?"

Hailey scanned the crowd in front of her, looking for possible targets. She spotted Atwater but nothing suspicious. "Allie Montgomery."

"What about her? CPD has told me she's off limits and she's undercover right now for a task force."

She arched an eyebrow. "Well I don't know about the off limits thing but she's back in Chicago."

Lynch groaned. "I've been wanting her for years."

"Now might be your chance."

"Why now?"

She shrugged. "Afghanistan might do her some good."

"You mean nine months in a place where she has to be herself the entire time and she can't just be someone else the next day?" Lynch said. He didn't become the SAC of Chicago area for the DEA by being dumb.

"Something like that."

"Hailey!" Kevin shouted.

She looked up to see the world about to go to hell and dove for the ground as soon as she saw the black van come around the corner. She had absolutely no cover. She couldn't get around the water foundation fast enough. She grabbed her weapon as they started shooting but she couldn't shoot back.

"Stay low," Chris Lynch said he covered her body.

And the bullets kept on coming.

* * *

 **AN: So... who's behind the drive-by's?  
**


	7. Chapter 7

She could hear shots from Atwater's 9mm firing back, two seconds later Lynch was on his feet and firing in the direction of the van but it was too late. It was gone. The only thing she could do was take out her radio to radio into Dispatch.

"Shots fired at plain clothed officers and civilians in Grant Park. Black Van," Hailey said into the radio.

Kevin ran over to her as she was standing up. He shook his head. "No plates. You okay?"

She nodded. "What the fuck was that?"

"Some brazen shooting," Lynch said. "This is now a joint investigation. You have the full resources of the DEA."

Hailey sighed. "Same van, twice in one day and same cop. What the hell are they after?"

Lynch holstered his weapon. "Who'd you piss off, Upton?"

Soon, everyone was on scene. Voight and Lynch shook hands. "We'll take it from here Chris, but thanks."

Lynch nodded. "If you need anything, just call. Upton, we'll talk."

Everyone stood around in a circle. "Two hits in one day. Gotta be personal," Antonio echoed what everyone was thinking.

"That's what I was afraid of," Voight said. "Who have you pissed off lately, Upton?"

She shrugged. "You're not doing you're job as a cop if you haven't pissed off a couple people."

"Humble brag," Ruzek said, lightening the mood a little. A few smiles were shared around the circle.

"I haven't really done any high profile cases lately or even been called to testify on any of the cases. If any criminal knows who I am, I'm impressed," Hailey said.

Kim spoke up. "What about Earl Brown?"

She shook her head. "That man will hate me until the day he dies. My testimony put him behind bars for 25 years and we all heard his name in the media smearing me, but my photo was never shown and he's not capable of pulling this type of heist off."

Jay also shook his head. "I don't think Brown has the creds to pull off a daytime drive by shooting on two cops and a federal agent. That takes guts."

"So we narrow it down to known criminal organizations. You did time in Gangs," Voight said.

"Five months before Robbery/Homicide and that was 3 years ago. Gangs don't have that long of a memory," Upton pointed out.

Voight sighed. "Atwater, call Wilson in Gangs. See what kind of chatter there has been. G-Park Lords, anything. After Montgomery and Halstead's visit this morning, I doubt they are behind this. Burgess, work with Platt and go through all of Upton's high profile, low profile cases that she was the lead detective on. Antonio, Ruzek and Montgomery, stay on the drug case and find out how that dope from San Diego got to Chicago. Find out some hard evidence that Williams' own dad killed him. We need answers on this one. Soon! Before more battery acid cut cocaine ends up here."

Hailey sighed. "And I'm benched."

He rolled his eyes. "You were benched before this and now you're most definitely benched. Halstead is going to take you home and babysit your ass so you don't get shot again!"

* * *

Hailey did not have a good night sleep that night, between the pain and wondering who was trying to kill her. She rolled around a lot that night, trying to find a comfortable position but really couldn't find one. She knew she was safe in her own home, between Jay sleeping beside her and Allie in the spare room nobody was going to get to her. There was an undercover car parked down the street. Nobody put a hit out on a Chicago Detective and expected to get away with it. Voight was going to make sure of that.

It was around 6 am when she woke up and decided that she was up for good. She went to go make coffee and the smell of her Keurig making her coffee, reminded her of the fact that she saw her sister in law working at Starbucks. And how very, very, very odd that was. Hannah was a stay at home mom to three kids, not someone who would be working at Starbucks. Unless her and Hailey's brother, Derek, really needed the money. Except the only reason they would need the money, is if Derek was into something stupid. He had a pretty good welding job in the rigs in North Dakota and he made some serious coin.

Hailey quietly went into her bedroom and got her phone from the charger and slipped out before waking Jay. She texted Platt, who would probably be the only one to do her request without asking Hailey too many questions of her method and what she was up to. _Can you run by brother, Derek Upton's, financials? Just a quick look._

However, Trudy Platt didn't text her back with what she found out on her fishing expedition, she called her. When Upton's phone buzzed with Platt's name on it, an hour later, Hailey knew that Platt had found something. "Good morning, Trudy," Hailey tried to sound upbeat.

"How many Oxycodone did Will Halstead prescribe you for you to sound this cheery this morning?" Platt shot back.

Hailey laughed. "None, and I'm guessing from this phone call that I'm not going to like what you found on this little drive-by either?"

Trudy Platt sighed. "Nope. Your brother is deep in debt. Just took out a second mortgage on the house, last week. That's all I could really do without getting a warrant on the financials. No reason for a second mortgage, the income from the oilfield is the same and it looks like there is an income coming in from Starbucks."

"Fuck," Hailey said. "This isn't good."

Platt sighed. "I'm guessing this has to do with the drive by shooting and not just to one up your brother?"

"You'd be correct. Let me devise a plan with Jay and Allie and I'll let Voight know what is going on."

"Sounds good, stay safe," Trudy said and hung up.

Jay came into the kitchen at that moment. "Devise a plan?" He put his own coffee cup into the Keurig to make a coffee for himself.

"How much did you hear of that conversation?"

Jay shrugged. "Enough to know that the only one to run a drive by on financials this early in the morning is Platt."

Hailey rose on her toes to kiss him. "Nobody said you weren't a good Detective."

He chuckled. "Nice deflection. What is this about?"

"Made Atwater stop at Starbucks yesterday and saw Hannah working there," she said.

Jay raised an eyebrow. He had met Hailey's brother's wife before. "As in Derek's wife, Hannah? Doesn't Derek make a decent living in the oilfield?"

Hailey nodded. "More than enough that Hannah doesn't have to work. Which got me thinking. This hit has to be personal. So I had Platt do a look see on their financials. Took out a second mortgage on their house last week."

Jay groaned. "Derek's in over his head on something."

Allie also came into the kitchen to make some coffee. "Derek's in over his head? Oh gee, imagine that."

"Good morning to you too," Hailey said, smiling though. No love was lost between Derek and Allie. Allie Montgomery had been a fixture at all holiday events since the day that Hailey and Allie had met at freshman orientation in University. Allie was straight from Florida and had no family in the Chicago area at the time and the Upton's, as dysfunctional as they were, took her in. However, Allie and Derek never really saw eye to eye on many subjects, and one of those major subjects was Allie's divorce.

Allie rolled her eyes. "What is this about?"

"Just a theory."

"I think we need to pay your brother a visit this morning," Jay said.

Allie held up her hands. "I'm out. Definitely out."

Hailey shook her head. "I need you as backup."

The brunette shook her head. "I love you, I love your family but I have had my fair share of Upton drama and dysfunction to last me a lifetime, thank you very much. I do not need to overflow my quota."

Hailey laughed. All of what Allie said was true so she didn't try and deny it. "Speaking of drama, your ex-husband texted me. You were by the other night. That somehow got left out. Logan's, the pub that you shouldn't have been at and then Adam's. Wow, Allie, you did fucking good."

* * *

Hailey, Jay, Allie and Adam met at Derek Upton's welding shop not long after she got off the phone with Platt. She had let Voight know what was going on, it was just a simple conversation with Derek. Adam was to remain in the car and make sure nothing was happening outside that shouldn't be happening and to catch anyone going to make a run for it. Allie was going to poke around the shop a little bit. Said ex-husband was a welder that had worked with Derek in the past so she knew her way around welding tools and could poke around safely. Jay and Hailey were going to go question Derek and see what the hell was going on.

Before they walked inside, Hailey gave her gun to Jay. "So I don't do anything stupid."

Jay raised an eyebrow. "I don't like the fact that you're not armed."

She rolled her eyes. She wasn't using the sling that April had gave her either, despite the fact that it was barely 24 hours after the shooting. "I have my backup on my ankle, like I always do."

He seemed satisfied with that answer so he took her gun at put it in his back waist as they walked towards where Derek's office was.

Hailey knocked on the door where Derek was on the phone and when he saw his little sister and her partner at the doorstep, he quickly got off the phone. He didn't stand up to greet them but he did smile. "Well, this is a surprise."

"It certainly is," she said, very frostily.

Derek was taken aback at her tone and got the memo that this wasn't a social visit, this was something way more serious than that. "What the fuck is going on for you to be visiting me during work hours? Especially with him?"

Hailey and Jay took a seat in the chairs across the desk from where Derek was sitting. She knew that this meeting was not going to go well and this might put her brother in prison, but that was a bridge she was going to cross later. She just wanted to know who wanted her dead at this moment. "I saw Hannah yesterday."

Derek shrugged. "So? She didn't mention anything."

"Working at Starbucks."

The dots started to connect for Derek, as he was not a dumb individual. "Oh."

"Made me wonder. Why my sister in law is working at Starbucks when I know what you make in a year. Definitely enough for her not to be working there in the middle of the day while your kids are at school, that's for sure," Hailey said.

Jay sighed. "We know you took a second mortgage out on the house last week."

"And somebody has tried to kill me twice in the two days," Hailey said. "And somehow I think this all leads back to you which I can't imagine that my straight laced brother would be messed up in something like this, but here we are, having this conversation."

Allie and Ruzek appeared in the doorway and all Hailey could think of was that she found something. She swallowed hard and made eye contact with Hailey and Jay before she spoke. Derek saw her in the doorway though.

"Stand up, Derek. You're under arrest. Put your hands behind your back," Allie ordered, as she walked over to him and put the handcuffs on his wrists, behind his back. "I haven't had to say this in a really long time, but you have the right to remain silent, anything you say can and will be used against you in a court of law, you have the right to an attorney and if an attorney can't be provided, one will be appointed for you."

* * *

 **AN: Sorry I've been MIA. I've been working TONS and when everything was going wrong in my life, the answer to my problems was a plane ticket so I've been hiding out. But I'm back, somewhat. So here's a chapter for you!**


	8. Chapter 8

**AN: My knowledge of courtrooms comes from Law and Order so...**

* * *

 **5 months later**

"The honorable Rita Clarke presiding," the court clerk read as the courtroom stood up as Judge Rita Clarke walked into the room. She was an older woman, stern but was considered fair. Prosecutors and defense attorneys liked being in her courtroom.

Judge Clarke sat down and looked through her glasses. "Derek Upton, this is a sentencing hearing. You are pleading guilty to two counts of felony drug trafficking of a controlled substance."

His lawyer, Jay Donaghue, nodded. "That is correct, your honor."

Judge Clarke also nodded. "Very well. Does the defense have any witnesses they will be calling?"

"The defense calls the arresting officer, former Chicago Police Department Detective and now DEA Agent Allison Montgomery." There were definitely whispers in the courtroom as normally cops testified for the state or prosecution, not the defense.

Allie walked up to the stand and took the oath and sat down and prepared herself for the possible onslaught that was going to come from the two lawyers. This was a high profile case, although it hadn't gone to trial, and a cop was testifying for the defense.

"Why are you testifying for the defense?" Jay Donaghue asked.

Allie looked at Jay directly in the eye. "Because Derek Upton helped me put Patrick Davis, a ruthless drug dealer, behind bars for good and helped Chicago PD Intelligence find the killers of Carl Williams and Martin Powell."

"What was Derek's role in Patrick Davis' crew?"

"He was the middle man. Derek was deep in gambling debts. Patrick Davis' cousin, a guy by the name of Ashton Walburg who went by the nickname Rabbit, was Derek's foreman. Rabbit heard about Derek's gambling debts and told him that if he moved some product around for him, he could get his gambling debts paid off. Derek then recruited two kids that worked for him at night, Carl Williams and Martin Powell, to sell it on the street."

Jay nodded. "Who did Derek owe?"

"A bookie by the name of Janny Ross."

"Janny Ross then put a hit out on Derek Upton's sister, Detective Hailey Upton, did he not?" Donaghue asked.

Allie thought it was a weird line of questioning for the defense but she went with it. "Yes, he did. The money was being wired directly from Patrick Davis' account, which is where we nailed him on, but Patrick only wired him $25,000 to cover half of Derek's debts."

"Did Derek fully cooperate with Chicago Police?"

Allie nodded. "He did."

"You knew Derek before you joined the Chicago Police Department. What can you tell me about him?"

"Objection, testimony," the prosecuting attorney, ASA Steve Kot, said.

Judge Clarke looked at Kot. "Overruled. She had a personal relationship with him before joining the Chicago Police Department, she can answer."

"I knew Derek through his sister, Detective Hailey Upton, and through my ex-husband, who was Derek's foreman for many years. I considered him to be a good husband and a good father," Allie said, hoping her face didn't give her disgrace of having to say that away. She told Donaghue when she agreed to testify for the defense, because Derek Upton did get her a rock solid case on Patrick Davis, but she was not commenting on her personal relationship with him and giving him a character statement, because she'd have no problem throwing him under the bus.

Donaghue saw the daggers being thrown at him by Allie and decided to wrap it up. "Thank you."

ASA Steve Kot stood up and faced Allie on the stand. "Who killed Carl Williams and Martin Powell anyways?"

Again, Allie thought that was an odd line of questioning. "Carl Williams' own father."

"Ever find the motive?"

"Sergeant Voight did get a confession, yes. I believe they were killed because they were dealing cocaine for Patrick Davis' crew and not their main supplier out of the G-Park Lords, Angel, who happened to be Williams' cousin."

Kot looked at her. "Why'd you testify for the defense? You helped get Derek Upton the plea deal but why testify for the defense. You certainly didn't say much about his character."

"Because it was his testimony against Rabbit and Patrick Davis that is going to throw away the key on Davis. I spent 18 months trying to bring him down and Derek Upton was the final nail in Patrick Davis' coffin."

Kot nodded. "Very well. How many other trials are you testifying at this week?"

Allie rolled her eyes, knowing exactly where Kot was going with this. She didn't just fly back from Afghanistan for this one trial. Derek Upton wasn't that special. "Three."

"Thank you," Steve said and nodded at the Judge to let her know he was done with Allie before sitting down.

Hailey and Jay watched from the back of the courtroom. They were there, as part of CPD, and as family. Hailey was not sure how well Allie's testimony was going to go, as she knew that Allie would absolutely not testify for Derek's character but she would testify in behalf of him doing her a solid on Patrick Davis. Both CPD Detectives were nervous on how Judge Clarke was going to sentence Derek.

"She did good," Jay whispered.

Hailey raised an eyebrow. "She stuck to her guns."

Once they had Derek in custody and he spilled his guts to Allie and Voight, it didn't take them long to unravel everything. Carl Williams and Martin Powell's killings, the hit put out on Hailey by Janny Ross, the gambling debts and how it all connected back to San Diego. It was actually Allie's ex-husband who gave them the smoking gun. The guy – Rabbit, who replaced Logan as Derek's foreman, was from San Diego, and Logan, said he had a questionable background but he was a hell of a welder so Derek overlooked it. Rabbit's cousin was Patrick Davis' and that was how battery acid cut cocaine that Allie was chasing in San Diego got on the streets of Chicago. Carl Williams and Martin Powell were working for Derek and Rabbit at night in the welding shop, trying to learn enough to see if they wanted to make a better life for themselves and go into the trades. They got sucked back into the lifestyle when Derek and Rabbit approached them about dealing on the side.

* * *

Jay, Hailey, Ruzek, Atwater, Burgess and Antonio ended up at Molly's after the day in the courtroom. Voight was the one who ended up having to testify for Kot's prosecution, something nobody in Intelligence wanted to do, given the fact that it was Hailey's brother who was pleading guilty to two felonies in a plea deal. They all needed a couple drinks after today. Judge Clarke would come back tomorrow with her sentencing for Derek.

"You know, we haven't been here together, in a really long time," Burgess commented.

Atwater nodded. "You're right. It's about damn time."

The door opened to Molly's and instinctively Jay put his arm around Hailey's waist as he heard the door open. To their surprise Allie Montgomery walked in the bar, with a half smile on her face as she approached the table of cops. It wasn't that busy in the bar, as it was a Wednesday and in the middle of the week. "Voight told me that I should probably show my face in here."

"Better than the bar in G-Park Lord territory that you were drinking your sorrows in 5 months ago," Ruzek commented.

Allie rolled her eyes. 'That was low. But I deserved that one."

Antonio grabbed her a drink from the bar. "Drinks are on us, for our favorite DEA Agent."

"Trying to drink all the alcohol you can before you go back to the dry land?" Jay teased as Allie accepted another beer from Hermann.

"Not actually a bad idea. Afghanistan really blows," Allie said as she took a sip of her beer. She turned to Hailey. "How are you holding up?"

Hailey shrugged, not wanting to give too much away in front of her co-workers. They knew it had been hard on her, even though Derek and her weren't super close but seeing any family in that situation is hard and being the one to put them behind bars is even worse. "I'm alright. I'll be better once this is all behind us."

"Amen to that," Jay said.

Allie smiled at her friend. "I think you got a good one. Might want to keep onto this guy."

Hailey smiled. "Oh I intend on it."

* * *

 **AN: Andddd we're done with this story. Honestly, I ran out of ideas for this but I knew it had to be wrapped up and this was the only thing that I could put on paper. I'm sorry it didn't have more Upstead moments. I am a lot better at writing one-shots so I will be back with those for Hailey and Jay.**


End file.
